2-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-imidazole | 700875-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-imidazole
• 英文别名: 2-p-methoxyphenyl-1-phenylsulfonyl-1H-imidazole；1-(benzenesulfonyl)-2-(4-methoxyphenyl)imidazole
• CAS: 700875-16-7
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: BYBTWHCSNKYAAY-UHFFFAOYSA-N

物化性质

• 熔点：
  79.5-80 °C
• 沸点：
  529.4±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-imidazole 在 氢溴酸 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 13.08h， 生成 4-(p-hydroxybenzoyl)-2-(p-hydroxyphenyl)-3H-imidazole
  参考文献：
  名称：

  Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=?a?ID=?a? Dedicated to Prof. G . Märkl on the occasion of his 75 th birthday

  摘要：

  The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of H-1 NMR data the tautomerism of aroylimidazolemethanones is described.

  DOI：

  10.1007/s00706-003-0085-2
• 作为产物：
  描述：

  苯磺酰氯 、 2-[4-(methyloxy)phenyl]-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到2-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=?a?ID=?a? Dedicated to Prof. G . Märkl on the occasion of his 75 th birthday

  摘要：

  The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of H-1 NMR data the tautomerism of aroylimidazolemethanones is described.

  DOI：

  10.1007/s00706-003-0085-2

文献信息

• Discovery of Novel 2-Aryl-4-benzoyl-imidazoles Targeting the Colchicines Binding Site in Tubulin As Potential Anticancer Agents
  作者：Jianjun Chen、Zhao Wang、Chien-Ming Li、Yan Lu、Pavan K. Vaddady、Bernd Meibohm、James T. Dalton、Duane D. Miller、Wei Li

  DOI：10.1021/jm100884b

  日期：2010.10.28

  A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4-carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl-thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogues have substantially improved aqueous solubility (48.9 mu g/mL for 5ga vs 0.909 mu g/mL for SMART-I, 0.137 mu g/mL for paclitaxel, and 1.04 mu g/mL for combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogues is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors.
• COMPOUNDS FOR TREATMENT OF CANCER
  申请人：Gtx, Inc.

  公开号：EP2608671B1

  公开（公告）日：2018-12-12